Muscalure

The sex attractant given off by the common housefly is an alkene named muscahtre. Propose a synthesis of muscalure starting from acetylene and any alkyl halides needed. What is the IUPAC name for muscalure ... 

Muscalure, structure of, 287 Mutarotation, 985-986 glucose and, 985-986 mechanism of. 986 Mycomycin, stereochemistry of, 330 Mylar, structure of, 819 n yo-Inositol, structure of, 135 Myrcene. structure of, 202 Mvristic acid, catabolism of, 1137 structure of. 1062... 

Muscalure 20, the pheromone of the housefly has been prepared from oleic acid or erucic acid, similarly (Z)-l 1-heneicosene 21, the synergist of muscalure was obtained [189]. The intermediate 22 for the pheromone of the Cabbage looper was prepared using (Z)-methyl-4-octenedioate [166bJ, that was obtained by partial ozonolysis of (Z,Z)-l,5-cyclooctadiene. Similarly disparlure 23, the sex attractant of the gypsy moth, has been synthesized by two successive crossed-couplings with (Z)-4-octene dioate [191],... 

Muscalure is the sex attractant of the common housefly (Musca domesticd). 

Another very important aspect of these transition metal-catalysed cross-coupling reactions stems from the high selectivity observed with stereo-defined vinyl sulfides. Applications to the stereoselective syntheses of pheromones were straightforward (see [321] and references therein), as shown in the two-step synthesis of muscalure from (Z)-l-bromo-2-phenylthioethylene [322] involving its sequential coupling through the bromo and phenylthio substituents with the appropriate derivatives. 

A sex pheromone was first demonstrated in the housefly by Rogoff et al. (1964), identified as (Z)-9-tricosene (muscalure) by Carlson et al. (1971) and shown to attract males in an olfactometer at doses as low as 0.07 pg by Adams and Holt (1987). Cis-9, O-epoxytricosane, (Z)-14-tricosen-10-one (Uebel et al., 1978) and methylalkanes (Uebel et al., 1976) are also components of the sex pheromone (Figure 8.1). Adams and Holt (1987) showed that each component has a different role in male courtship behavior. (Z)-9-Tricosene increases male mating-strike activity toward females. The epoxide and ketone decrease the number of homosexual mating strikes, thus acting as sex-recognition factors. The methyl-branched alkanes act as an arrestant and increase the amount of time a male spends with a treated model. 

A number of studies since 1980 have concentrated on the search for a sex pheromone analogous to Muscalure, the first contact pheromone discovered in mature Musca domestica females (Carlson et al., 1971). Other hydrocarbons have been described in various Diptera (Carlson et al., 1978 Blomquist and Jackson, 1979 El Messoussi et al., 1994 Blomquist, Chapter 8, in this volume). In all cases, a cuticular hydrocarbon with low or no volatility and high abundance was necessary, but not sufficient for a response. Its action could be checked only... 

Musca domestica, with its female-specific Muscalure - (Z)-9-tricosene - was first used as a model for biosynthetic studies (Blomquist and Jackson, 1979 Blomquist et al., 1987). Inspired by these model studies, Jallon (1984) proposed and discussed the first hypothetical pathway for the biosynthesis of major cuticular... 

Darbro, J.M., Millar, J.G., McElfresh, J.S. and mullens, B.A. (2005). Survey of muscalure [(Z)-9-tricosene] on house flies (Diptera Muscidae) from field populations in California. Environ. Entomol., 34, 1418-1425. 

Z)-9-Tricosene 382 (muscalure) together with a series of homologous alkenes was isolated as the sex-specific attractive basic component from faecal and cuticular lipids of the house fly Musca domestica 219). These alkenes, all possessing (Z)-configuration, were, in addition to other methods, synthesized by selective Wittig ole-... 

Octyl acrylamide thiocyanate octhilinone Oleyl alcohol muscalure Ortho see Parent compound... 

Pentylamine pendimethalin Pentyl bromide muscalure Pentyl chloride hexaconazole Pentyl magnesium bromide muscalure... 

MCPA-thioethyl methoxyphenone muscalure 2 phenyl phenol piperonyl butoxide... 

Alkenes are hydrocarbons with carbon-carbon double bonds. Alkenes are sometimes called olefins, a term derived from olefiant gas, meaning oil-forming gas. This term Introduction originated with early experimentalists who noticed the oily appearance of alkene derivatives. Alkenes are among the most important industrial compounds (see Section 7-6), and many alkenes are also found in plants and animals. Ethylene is the largest-volume industrial organic compound, used to make polyethylene and a variety of other industrial and consumer chemicals. Pinene is a major component of turpentine, the paint solvent distilled from extracts of evergreen trees. Muscalure (cw-tricos-9-ene) is the sex attractant of the common housefly. 

Muscalure, the sex attractant of the common housefly, is cA-tricos-9-ene. Most syntheses of alkenes give the more stable trans isomer as the major product. Devise a synthesis of muscalure from acetylene and other compounds of your choice. Your synthesis must give specifically the cis isomer of muscalure. 

The name muscalure comes from the generic name of the house-fly, Musca,... 

We will start by looking at two syntheses of the very simple pheromone of a very common insect—the house-fly. The pheromone, known as muscalure, is a Z-alkene. 

One approach, used by some American chemists in the early 1970s, was very simple. These chemists noted the similarity between the structures of muscalure and the fatty acid known as erucic acid, which is abundant in rapeseed oil, and decided to make muscalure from erucic acid. They first reacted the acid with two equivalents of methyllithium—the first equivalent deprotonates the acid to make a lithium carboxylate salt, while the second reacts with the lithium carboxylate to make a ketone. 

The next step is to remove the ketone functional group. You met a few ways of doing this in the last chapter here the method chosen was to make a hydrazone and heat in the presence of base. Muscalure is the product. 

By stirring the alkyne with Lindlar s catalyst under an atmosphere of hydrogen they were able to make muscalure. 

House-flies are irritating and a minor health hazard, but the cotton boll weevil is an enormously destructive pest of the American cotton crop and is responsible for vast economic losses. The weevil has a pheromone called grandisol. The structure and synthesis of grandisol are rather more complicated than the syntheses of muscalure, but all the reactions are ones you have met in the first 24 chapters of the book. 

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